So here I am, a hot single mom looking for love, and it’s not easy with a kid in tow. Having a child stops me from taking the usual kinds of risks — I can’t follow the tried and tested way of finding a boyfriend that worked before I was a mother (getting trashed at a bar or club and ending up lip-locked with a handsome stranger). So what’s a girl to do?
Jumping back into the dating pool can be really hard, says Dr. Tina B. Tessina, a licensed psychotherapist and author of The Unofficial Guide to Dating Again (John Wiley & Sons). “If you haven’t dated for a long time, you can feel like a stranger in a strange land. If you connected with your prior relationship at a young age, you may not know how to date as a grown-up,” says Dr. Tessina. “It’s like going through adolescence all over again.”

That’s my problem. When I met my ex-husband, I was 22 and just out of university, and now I’m a grown woman with my life pretty together and a baby on my hip. I know what I want and I think I know how to get it, but I’m scared silly at every stage in the dating game. Here’s why:

challenge #1 – meeting eligible men

Going to a bar with fingers crossed just doesn’t cut it anymore. Investing $40 in a sitter before I’m even out the door means I want to stack the odds in my favour to get value from the money I will spend during a date.

Internet dating sounded ideal but wasn’t. I wrote my ad and waited for the men to beat down my door, but it didn’t happen. I tried Lavalife, eHarmony and Nerve personals, getting no more than a few awkward coffee dates with well-intentioned guys that I just couldn’t imagine getting jiggy with.

My Internet dating escapades made me feel desperate and unattractive, especially when the only hot guy to contact me said he was only interested in a little fun with single moms — relationship-wise they just weren’t his type.

Solution: Dr. Tessina recommends what she calls the “Get a life” method of dating, where you go to places and do things that interest you intrinsically, and meet others who are interested in similar things. “Making friends is both easier and more successful than dating,” she says, and I can relate to that, because sometimes sitting across from a date is harder than listening to my baby scream for two hours.

Asking friends to hook me up has had mixed results. Some friends interpret my “know any great single guys?” question as an excuse to set me up with anything with a pulse, but I’ll admit it has garnered a few interesting dates. Apparently, this method can be very effective so long as you are clear about what you are looking for, says Sharon McKenna, author of Sex and the Single Mom: The Essential Guide to Dating, Mating and Relating (Ten Speed Press).

“Let your friends know that you are open to meeting someone,” says McKenna. “But be careful not to sound too desperate and set some boundaries. That way, they’ll feel comfortable trying to pair you up with someone and know exactly what you are looking for, as well as what you aren’t.”

Challenge #2 – loving my post-baby body

Assuming that I could actually 1) meet someone I like enough to contemplate getting into bed with and 2) find someone I could convince to baby-sit for a whole night, I have a whole big batch of mommy neuroses to consider.

I’m still nursing so my boobs are off-limits, I think. I have a C-section scar and my belly jiggles now. Even though I’ve lost the baby weight, I know my body is never going to look the same.

Solution: “Some women feel proud of their post-baby body, but many don’t want to be naked,” says McKenna. “The healthiest place to be is somewhere in the middle, where you’re embracing the sensual side of having given birth but working hard to change the stuff you’re unhappy about.”

Challenge #3 – fessing up

When Mr. Right comes along, he has to understand that I can’t do spur-of-the-moment, and romantic weekends away are impossible. Worse than that, he needs to be okay with being second-best in my life. Because of these reasons and more, I usually blurt that I have a kid as soon as I meet someone. Unfortunately, this makes a lot of men run for the hills. Tempting as it is to not mention my child until I have to, I know it’s the right thing to do.

Solution: “You have to tell your date you have a child ASAP,” says Dr. Tessina. “Unless you’re just interested in fooling around, you need to know how your date feels about your kids.”

McKenna agrees, saying that by hiding your motherdom you are lowering your standards in order to find a bigger pool of potential dates. “It’s just part of life as a single parent that some people won’t want to get involved, and you don’t want to be with someone who is so rigid that they won’t date someone with children.” So really, if a date bails when you tell him about your child, he’s doing you a favour — it wouldn’t have worked out anyway.

Challenge #4 – introducing my child

I have a strong urge to put all potential suitors to the test by seeing how they act around my child, so I can separate the wheat from the chaff straight away, but I don’t want my daughter to meet a succession of her mummy’s “special friends” and be scarred for life in some way.

Solution: When I decide the time is right to introduce a new boyfriend to my child, Dr. Tessina suggests introducing him as a friend and acting accordingly. “When you are both with the children, make sure the activity is about the kids, as your children will feel more comfortable with the person without the additional pressure of knowing about your relationship,” she says.

Challenge #5 – avoiding weirdos

After enduring my longest dry spell ever (15 months and counting), it can be tempting to give guys more consideration than I would have in my pre-baby years. Not that I had stellar taste in men (I’m a single mom for good reason), but considering how I’m looking for so much more as a mother than I was as a single young thing, I need to be more picky, not less.

Solution: McKenna says when you become a mom, your bad-guy warning system needs to be on red alert, because the emotional costs of being treated badly are so much higher: single moms don’t have time to lick their wounds or get depressed over bad relationships.

“Avoid a bad end by getting it right from the start,” says McKenna. You do this by listening hard to what a date has to say and paying close attention to how he treats others. Look for any major personality flaws and go with your gut, especially when anything is said in reference to children. Jennifer Aikman, a Vancouver single mom, has met her share of strange dates, and finds it especially uncomfortable when they are overly interested in her daughter. “Open and interested is good,” she says. “Offering to baby-sit is creepy.”

With all these considerations in mind, I’m bravely attempting to get out of my dry spell and setting forth in my efforts to one day get kisses from someone other than just my child. Tough as it is, I know there has to be a good guy out there just waiting for a woman like me to enrich his life. I just wonder how many frogs I’ll have to kiss before I find my prince, and whether he could love my daughter as much as he loves me.

Lola Augustine Brown, a British-born, B.C.-based writer is finding dating as a single mom terrifying and exciting all at once.